Cyclopentylamine → N6-Cyclopentyladenosine

HRID 923705Notes

Reaction equation

HRID 923705 reaction equation
Cl[C:2]1([NH2:20])[N:19]=[CH:18][N:17]=[C:16]2[C:3]1=[N:4][CH2:5][N:6]2[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[CH:21]1(N)[CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)C>[CH:21]1([NH:20][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:16]=3[N:17]=[CH:18][N:19]=2)[C@@H:7]2[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 666015536-Chloroadenosine

Product 1

HCID 657378N6-CyclopentyladenosineYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
8 °C

Procedure

Step 1: 1 Liter of ethanol was charged into a reactor and stirred rapidly. 0.3 kg of 6-chloroadenosine and 0.267 kg of cyclopentylamine were added to the ethanol in the reactor. The reactor was heated to reflux for 2 hr, then cooled to 8 degrees C. and kept under these conditions for 12 hours. The crystallized material was filtered from the mother liquid and the solid cake was washed with 0.33 L of ethanol to produced a wet cake. The wet cake was dried to obtain N6-cyclopentyladenosine (0.249 kg).

Workup

  1. temperatureThe reactor was heated
  2. temperatureto reflux for 2 hr
  3. filtrationThe crystallized material was filtered from the mother liquid
  4. washthe solid cake was washed with 0.33 L of ethanol
  5. customto produced a wet cake
  6. customThe wet cake was dried

Sources & evidence

ORD record
ord-ea079551b8b94925bc21418a8132f243
Source dataset
uspto-grants-2016_03
Patent number
US09278991B2

Reaction notes

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